In February 2020, “newly resurfaced” video of Mike Bloomberg purportedly showing the former New York City mayor describing transgender women as “some guy in a dress” and using “it” in lieu of a pronoun appeared just ahead of a final round of Democratic Party debates:
On February 18 2020, the New York Post published an item titled “Mike Bloomberg referred to trans women as ‘it’ and ‘some guy in a dress,'” describing a “newly unearthed” clip before indicating it was filmed less than a year earlier in March 2019:
A newly unearthed video shows 2020 presidential hopeful Mike Bloomberg referring to transgender women for a second time as “some guy in a dress.”
After a new campaign ad touted the former mayor as “incredibly sensitive” to the LGBTQ community, a video resurfaced of Bloomberg last year referring to transgender people as “he, she or it” and “some guy in a dress” — the second time he’s been caught making such comments in recent years.
In the clip, recorded in March  before he announced his campaign, Bloomberg used the language to warn 2020 Democratic hopefuls against stressing transgender issues, arguing that they wouldn’t play well in Middle America … He delivered a similar remark about a “man wearing a dress” while making the same point at Oxford University in 2016.
As noted in the Post, Bloomberg made remarks similar to the “newly surfaced” clip in 2016:
Multiple clips of Bloomberg describing transgender people as “it” and again calling transgender women “some guy in a dress” circulated on YouTube on February 18 2020:
BuzzFeed News reported on the 2019 remarks, providing a date and context for them. Also included was a longer version of the video and larger context for the discussion; Bloomberg made the remarks around the 12-minute, 45-second mark:
Bloomberg’s sensitivity [to the LGBTQ community] was far less apparent at a forum hosted by the Bermuda Business Development Agency on March 21, 2019, in Manhattan, where Bloomberg derided Democratic candidates for talking about transgender protections.
“If your conversation during a presidential election is about some guy wearing a dress and whether he, she, or it can go to the locker room with their daughter, that’s not a winning formula for most people,” he said.
Bloomberg made a similar remark about a “man wearing a dress” in 2016, but his comments uncovered [on February 18 2020] — remarks he made less than a year [prior] — came amid the early stages of the 2020 Democratic primary.
The video was posted to YouTube shortly after the March  event, but has received few views. Bloomberg was not a candidate for president at the time, but announced his campaign just eight months after he made the remarks.
Before the 2019 video circulated, Bloomberg drew scrutiny for having made similar remarks in 2016. In the first of the two clips above, Bloomberg spoke in England on December 8 2016, and said:
If you want to know if somebody is a good salesman, give him the job of going to the Midwest and picking a town and selling to that town the concept that some man wearing a dress should be in a locker room with their daughter… if you can sell that, you can sell anything. They just look at you and they say, ‘What on Earth are you talking about?’
Multiple tweets and Facebook posts referenced “newly resurfaced” video of Mike Bloomberg making the “some guy in a dress” and “it” comments about transgender people. Although there were two known sets of remarks, the “unearthed” version was not very old — having taken place in 2019. The quotations were accurate, and the claim is true.